CN107129471B - Organic compound, organic photoelectric device and display device - Google Patents
Organic compound, organic photoelectric device and display device Download PDFInfo
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- CN107129471B CN107129471B CN201710088444.9A CN201710088444A CN107129471B CN 107129471 B CN107129471 B CN 107129471B CN 201710088444 A CN201710088444 A CN 201710088444A CN 107129471 B CN107129471 B CN 107129471B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 54
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- 230000000903 blocking effect Effects 0.000 claims description 16
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- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 230000005693 optoelectronics Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 229910052741 iridium Inorganic materials 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 125000004306 triazinyl group Chemical group 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- YFCSASDLEBELEU-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene-11,12,15,16,17,18-hexacarbonitrile Chemical compound N#CC1=C(C#N)C(C#N)=C2C3=C(C#N)C(C#N)=NN=C3C3=NN=NN=C3C2=C1C#N YFCSASDLEBELEU-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000005103 alkyl silyl group Chemical group 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 3
- 239000005441 aurora Substances 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
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- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
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- 229910010272 inorganic material Inorganic materials 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
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- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- JRGGUPZKKTVKOV-UHFFFAOYSA-N 1-bromo-3-chlorobenzene Chemical compound ClC1=CC=CC(Br)=C1 JRGGUPZKKTVKOV-UHFFFAOYSA-N 0.000 description 1
- UYYNISZZEVRNCF-UHFFFAOYSA-N 2-(4-bromophenyl)-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC=NC=N1 UYYNISZZEVRNCF-UHFFFAOYSA-N 0.000 description 1
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- MTUBTKOZCCGPSU-UHFFFAOYSA-N 2-n-naphthalen-1-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 MTUBTKOZCCGPSU-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Abstract
The invention relates to an organic compound, an organic photoelectric device and a display device, and particularly discloses an organic compound represented by chemical formula 1, an organic photoelectric device including the organic compound, and a display device including the organic photoelectric device.
Description
Citations to related applications
This application claims priority and benefit to korean patent application No. 10-2016-0023669, filed by the korean intellectual property office at 26/2/2016, the entire contents of which are incorporated herein by reference.
Technical Field
The application discloses an organic compound, an organic photoelectric device and a display device.
Background
An organic photovoltaic device is a device that converts electrical energy into light energy and vice versa.
The organic photoelectric device may be classified as follows according to its driving principle. One is an optoelectronic device in which excitons are generated from light energy, separated into electrons and holes, and transported to different electrodes to generate electric energy, and the other is a light-emitting device in which a voltage or current is supplied to the electrodes to generate light energy from the electric energy.
Examples of the organic photoelectric device may be an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.
Among them, Organic Light Emitting Diodes (OLEDs) have recently attracted attention due to an increase in demand for flat panel displays. The organic light emitting diode converts electric energy into light by applying current to an organic light emitting material and has a structure in which an organic layer is interposed between an anode and a cathode.
The performance of an organic light emitting diode may be influenced by the characteristics of the organic layers and, among other things, may be influenced mainly by the characteristics of the organic materials of the organic layers. In particular, there is a need to develop an organic material capable of increasing hole and electron mobility and simultaneously increasing electrochemical stability so that the organic light emitting diode can be applied to a large-sized flat panel display.
Disclosure of Invention
An embodiment provides an organic compound capable of realizing an organic photoelectric device having high efficiency, long life, and low driving voltage.
Another embodiment provides an organic photoelectric device including the organic compound.
Still another embodiment provides a display device including the organic photoelectric device.
According to one embodiment, there is provided an organic compound represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
R1to R4Independently of each other is hydrogen or deuterium,
l is composed of1-L2-L3-L4The-is represented by (a) a,
L1to L4Independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heteroarylene group, with the proviso that L1To L4Is a substituted or unsubstituted C6 to C20 arylene group,
Ar1is a substituted C2 to C20 heteroaryl group,
n1 is an integer of 5, and
n2 to n4 are independently integers of 4.
Another embodiment provides an organic photoelectric device including an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the organic layer contains the organic compound.
Still another embodiment provides a display device including the organic photoelectric device.
An organic photoelectric device having high efficiency, long life, and low driving voltage can be realized.
Drawings
Fig. 1 to 4 are cross-sectional views illustrating an organic light emitting diode according to an embodiment.
< description of symbols >
100, 200, 300, 400: organic light emitting diode
105: organic layer
110: cathode electrode
120: anode
130: emissive layer
140: hole transport layer
141: hole injection layer
150: electron transport layer
151: electron injection layer
152: hole blocking layer (Electron transport auxiliary layer)
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto and is defined by the scope of the claims.
In the present specification, when a definition is not otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is substituted by deuterium, halogen, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C6 to C30 heterocyclic group, a C1 to C20 alkoxy group, a fluorine group, a C1 to C10 trifluoroalkyl group such as a trifluoromethyl group, or a cyano group. In one example of the present invention, "substituted" means substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C6 to C30 heterocyclic group, in place of at least one hydrogen of the substituent or compound. In one example of the invention, "substituted" means substituted with deuterium, a C1 to C10 alkyl group, a C6 to C30 aryl group, a C6 to C30 heterocyclyl group, in place of at least one hydrogen of the substituent or compound.
Further, a substituted halogen, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C6 to C30 heterocyclic group, a C1 to C20 alkoxy group, a fluorine group, a C1 to C10 trifluoroalkyl group such as a trifluoromethyl group, or two adjacent substituents of a cyano group may be fused to each other to form a ring. For example, a substituted C6 to C30 aryl group may be fused with another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.
In the present specification, when a specific definition is not otherwise provided, "hetero" means that at least one heteroatom selected from the group consisting of N, O, S, P and Si, and the remaining carbon atoms are included in one functional group.
In the present specification, "aryl group" means a non-aromatic fused ring having at least one hydrocarbon ring aromatic moiety, and generalized hydrocarbon ring aromatic moieties connected by single bonds, and including directly or indirectly fused hydrocarbon ring aromatic moieties. The aryl group can be a group that is a monocyclic, polycyclic, or fused polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional group.
In this specification, "heterocyclic group" includes heteroaryl groups, and includes groups selected from N, O, S. At least one heteroatom of P, and Si replaces a cyclic compound, such as an aryl group, a cycloalkyl group, a fused ring, or a combination thereof. When the heterocyclic group is a fused ring, each or all of the rings of the heterocyclic group may include at least one heteroatom.
More specifically, the substituted or unsubstituted C6 to C30 aryl group and/or the substituted or unsubstituted C2 to C30 heterocyclic group means a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted phenylthio group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted oxadiazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or, A substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, combinations thereof, or fused rings of combinations of the foregoing, but are not limited thereto.
In the present specification, a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group means a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group which is defined above and has two points of attachment, for example, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted tetracenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted tetrabiphenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryleneene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted furyleneene group, A substituted or unsubstituted thienylene group, a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolylene group, a substituted or unsubstituted oxazolylene group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolylene group, a substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted benzofuranylene group, a substituted or unsubstituted benzothienylene group, a substituted or unsubstituted benzimidazolylene group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolylene group, A substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted quinoxalylene group, a substituted or unsubstituted naphthyrylene group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinylene group, a substituted or unsubstituted phenazinylene group, a substituted or unsubstituted phenothiazinylene group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a combination of the foregoing groups, but is not limited thereto.
In this specification, the hole characteristics refer to the ability to give electrons to form holes when an electric field is applied, and holes formed in the anode can be easily injected into the light-emitting layer and holes formed in the light-emitting layer can be easily transported into the anode and transported in the light-emitting layer due to the conduction characteristics according to the Highest Occupied Molecular Orbital (HOMO) level.
Further, the electronic characteristics refer to an ability of receiving electrons when an electric field is applied, and electrons formed in the cathode may be easily injected into the light emitting layer due to a conduction characteristic according to a Lowest Unoccupied Molecular Orbital (LUMO) level, and electrons formed in the light emitting layer may be easily transported into the cathode and transported in the light emitting layer.
Hereinafter, an organic compound according to an embodiment is described.
The organic compound according to one embodiment is represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
R1to R4Independently of each other is hydrogen or deuterium,
l is composed of1-L2-L3-L4The-is represented by (a) a,
L1to L4Independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heteroarylene group, with the proviso that L1To L4Is a substituted or unsubstituted C6 to C20 arylene group,
Ar1is a substituted C2 to C20 heteroaryl group,
n1 is an integer of 5, and
n2 to n4 are independently integers of 4.
The organic compound represented by chemical formula 1 includes a 9, 9-diphenylfluorene structure, a substituent having an electronic characteristic, and a linking group (including an arylene group or an arylene group) between the 9, 9-diphenylfluorene structure and the substituent having an electronic characteristic. The linking group can increase the flexibility of the compound and further impart excellent morphological characteristics thereto, thereby playing a significant role in achieving high efficiency, long life, and low driving voltage in an organic photoelectric device.
Further, a substituent having an electronic property necessarily includes another substituent, and thus, compared to a substituent having an electronic property but not substituted, it is possible to protect the weakest part of the heterocycle and thus improve heat resistance.
Further, with respect to the 9, 9-diphenylfluorene structure in the organic compound according to an embodiment, carbon atoms constituting a ring other than the ring including the linking group form a bond with hydrogen or deuterium, in addition to other carbon atoms, but there is no other substituent. Such a structure may facilitate the design of molecules with low molecular weight and high energy T1, as compared to molecules that are otherwise substituted with fluorine, and ultimately ensure improved properties and thermal stability of the material.
Ar1May be a substituted C2 to C20 heteroaryl group,and the heteroaryl group includes at least two nitrogen atoms.
In the examples of the present invention, Ar1May be a substituted pyrimidinyl group, a substituted triazinyl group, a substituted quinazolinyl group, or a substituted isoquinazolinyl group. In the examples of the present invention, Ar1There may be specifically mentioned a substituted triazinyl group, a substituted quinazolinyl group, or a substituted isoquinazolinyl group, and a substituted or unsubstituted triazinyl group. The reacting at Ar may be performed by one selected from deuterium, a C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 allyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof1The substituents described in the definitions of (a) and (b), and in embodiments of the invention, substituted or unsubstituted C6 to C30 aryl groups may be used.
For example, Ar1May be represented by one selected from chemical formulas 2 to 6.
In the chemical formulae 2 to 6,
R5to R12Independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.
Due to these structural characteristics, the organic compound according to an embodiment may have excellent heat resistance.
When the substituents represented by chemical formulas 2 to 6 are included as the substituents having electronic characteristics, the organic compound may have LUMO of-2.0 eV to-1.7 eV and show excellent electronic characteristics compared to a compound not including pyridine or a nitrogen atom.
R5To R12May independently be a substituted or unsubstituted C6 to C20 aryl group.
For example, when R is5To R12Independently a substituted or unsubstituted C6 to C20 aryl group, a cyclic or unsubstituted C6 to C20 arylThe phenyl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted pyrenyl group, but is not limited thereto.
L may be represented by one selected from the group consisting of chemical formula L-1 through chemical formula L-7.
In the chemical formulae L-1 to L-7,
R13to R17Independently a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
m1 to m3 and m5 are independently integers of 0 to 4,
m4 is an integer of 0 to 3.
The organic compound represented by chemical formula 1 includes a 9, 9-diphenylfluorene structure, a substituent having an electronic characteristic, and a linking group (including an arylene group or an arylene group) between the 9, 9-diphenylfluorene structure and the substituent having an electronic characteristic.
In particular, when the organic compound according to one embodiment has the linking group represented by the chemical formulae L-1 to L-7 as the linking group, the linking group may increase flexibility of the compound or finely adjust its respective characteristics, thus imparting more appropriate morphological characteristics thereto and thus playing an important role in realizing high efficiency, long life, and low driving voltage of the organic photoelectric device. In one embodiment of the invention, L may be L-2, L-4, or L-5, and desirably L-2 or L-4. The organic compound according to an embodiment may be represented by one selected from chemical formula 2-1 to chemical formula 2-24, chemical formula 3-1 to chemical formula 3-24, chemical formula 4-1 to chemical formula 4-24, chemical formula 5-1 to chemical formula 5-23, chemical formula 6-1 to chemical formula 6-23 of [ group 1], but is not limited thereto (the hetero atoms of the specific compounds of [ group 1] are all "N").
[ group 1]
The organic compound can be applied to an organic photoelectric device.
The organic compound can be applied to an organic photoelectric device alone or as a mixture with other organic compounds. The organic compound is used as a composition together with other organic compounds.
Hereinafter, an organic photoelectric device including the organic compound is described.
The organic photoelectric device may be any device that converts electric energy into light energy, and vice versa, without particular limitation, and may be, for example, an organic photodiode, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.
The organic photoelectric device may include an anode and a cathode facing each other, at least one organic layer between the anode and the cathode, and the organic layer contains the organic compound.
For example, the organic layer includes a hole transport layer, an electron transport layer, and an emission layer between the hole transport layer and the electron transport layer, and the organic compound may be contained in the electron transport layer.
For example, the organic layer includes a hole transport layer, an electron transport layer, and an emission layer between the hole transport layer and the electron transport layer, and the organic compound may be contained in the emission layer.
For example, an organic compound may be used as a host in the emission layer.
For example, the organic layer further includes a hole transport layer, an electron transport layer, an emission layer between the hole transport layer and the electron transport layer, and an electron transport auxiliary layer (hole blocking layer) between the emission layer and the electron transport layer, and the organic compound may be contained in the electron transport auxiliary layer.
Herein, an organic light emitting diode is described as one example of an organic photoelectric device with reference to the accompanying drawings.
Fig. 1 to 4 are cross-sectional views illustrating an organic light emitting diode according to each embodiment.
Referring to fig. 1, an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110 and an organic layer 105 between the anode 120 and the cathode 110.
The anode 120 may be made from a conductor with a larger work function to aid hole injection, and may be, for example, a metal, metal oxide, and/or conductive polymer. The anode 120 may be, for example, metallic nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; combinations of metals and oxides, e.g. ZnO and Al or SnO2And Sb; conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thiophene) (PEDT), polypyrrole, and polyaniline, but are not limited thereto.
The cathode 110 may be made from a conductor having a smaller work function to aid in electron injection and may be, for example, a metal oxide, and/or a conductive polymer. The cathode 110 may be, for example, a metal or alloy thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or the like; multilayer materials such as LiF/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2But not limited thereto,/Ca.
The organic layer 105 includes an organic compound.
Referring to fig. 2, an organic light emitting diode 200 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 between the anode 120 and the cathode 110, and the organic layer 105 includes an emission layer 130, a hole transport layer 140, and an electron transport layer 150.
The emission layer 130 is interposed between the hole transport layer 140 and the electron transport layer 150, and may include the organic compound.
The emission layer 130 may include the organic compound as a host, and may include a single organic compound, at least two organic compounds, or a mixture of an organic compound and other organic compounds.
The emission layer 130 may further include a dopant. The dopant may be a red, green or blue dopant, for example a phosphorescent dopant.
The dopant is mixed with the first host compound and the second host compound in a small amount to cause light emission, and may be generally a material such as a metal complex which emits light by being excited to a triplet state or more a plurality of times. The dopant may be, for example, an inorganic, organic, or organic/inorganic compound, and one or more of them may be used.
The phosphorescent dopant may be an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by formula Z, but is not limited thereto.
[ chemical formula Z ]
L2MX
In formula Z, M is a metal, and L and X are the same or different and are ligands used to form a coordination compound with M.
M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L and X can be, for example, bidentate ligands.
The emission layer 130 may be formed using a dry film forming method or a solution method. The dry film forming method may be, for example, a Chemical Vapor Deposition (CVD) method, sputtering, plasma plating, and ion plating, and two or more compounds may be simultaneously formed into a thin film or compounds having the same deposition temperature may be mixed and formed into a thin film. The solution process may be, for example, ink jet printing, spin coating, slot coating, rod coating, and/or dip coating.
Referring to fig. 3, an organic light emitting diode 300 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 between the anode 120 and the cathode 110, the organic layer 105 includes an emission layer 130, a hole transport layer 140, an electron transport layer 150, a hole injection layer 141 between the anode 120 and the hole transport layer 140, and an electron injection layer 151 between the cathode 110 and the electron transport layer 150, and the emission layer 130 or the electron transport layer 150 includes the organic compound.
Referring to fig. 4, an organic light emitting diode 400 according to an embodiment includes an anode 120 and a cathode 110, and an organic layer 105 between the anode 120 and the cathode 110, the organic layer 105 includes an emission layer 130, a hole transport layer 140, an electron transport layer 150, a hole injection layer 141 between the anode 120 and the hole transport layer 140, and an electron injection layer 151 between the cathode 110 and the electron transport layer 150, and an electron transport auxiliary layer (hole blocking layer) 152 between the emission layer 130 and the electron transport layer 150, and the emission layer 130, the electron transport layer 150, or the electron transport auxiliary layer (hole blocking layer) 152 includes the organic compound.
The hole injection layer can improve the interfacial property between ITO as an anode and an organic material for a hole transport layer, and is applied to non-planarized ITO, thereby planarizing the surface of the ITO. For example, hole injection layersA material having an intermediate value between the work function of ITO and the HOMO of the hole transport layer, particularly a desired conductivity, may be contained to adjust the difference between the work function of ITO as an anode and the HOMO of the hole transport layer. In connection with the present invention, the hole injection layer may include N4, N4' -biphenyl-N4, N4' -bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4, 4' -diamine), but is not limited thereto. In addition, the hole injection layer may further include a conventional material, for example, copper phthalocyanine (CuPc), an aromatic amine such as N, N ' -dinaphthyl-N, N ' -phenyl- (1,1' -biphenyl) -4,4' -diamine (NPD), 4',4 ″ -tris [ methylphenyl (phenyl) amino group]Triphenylamine (m-MTDATA), 4' -tris [ 1-naphthyl (phenyl) amino]Triphenylamine (1-TNATA), 4' -tris [ 2-naphthyl (phenyl) amino]Triphenylamine (2-TNATA), 1,3, 5-tri [ N- (4-biphenylaminophenyl) phenylamino]Benzene (p-DPA-TDAB), and compounds such as 4,4' -bis [ N- [4- { N, N-bis (3-methylphenyl) amino } phenyl]-N-phenylamino]Biphenyl (DNTPD), hexaazatriphenylene-hexacarbonitrile (HAT-CN), etc., polythiophene derivatives such as poly (3, 4-ethylenedioxythiophene) -poly (styrenesulfonic acid (PEDOT) as conductive polymers
To
Is coated on, for example, ITO as an anode.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the anode 120 by any of various methods, for example, vacuum deposition, spin coating, casting, Langmuir-blodgett (lb) method, and the like.
When the hole injection layer is formed using vacuum deposition, vacuum deposition conditions may vary depending on a material used to form the hole injection layer, and desired structural and thermal properties of the hole injection layer to be formed, and may be, for example, 10 ℃ at a temperature of 100 ℃ to 500 ℃-8Bracket to 10-3The vacuum deposition is performed at a pressure of torr, and a deposition rate of 0.01 to 100 c/sec, but the deposition conditions are not limited thereto.
When the hole injection layer is formed using spin coating, the coating conditions may vary depending on the material used to form the hole injection layer, and the desired structure and thermal properties of the hole injection layer to be formed. For example, the coating rate may be 2000rpm to 5000rpm, and the temperature at which heat treatment is performed to remove the solvent after coating may be 80 ℃ to 200 ℃, but the coating conditions are not limited thereto.
The conditions for forming the hole transport layer and the electron blocking layer may be defined based on the above-described formation conditions for the hole injection layer.
The thickness of the hole transport region may be
To
For example,
to
When the hole transport region includes a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be
To
For example
To
And the hole transport layer may have a thickness of
To
For example
To
When the thicknesses of the hole transport region, the HIL, and the HTL are within these ranges, satisfactory hole transport characteristics can be obtained without a large increase in driving voltage.
In addition to the materials as described above, the hole transport region may further include a charge generation material to improve conductivity. The charge generation material may be uniformly or non-uniformly dispersed in the hole transport region.
The charge generating material may be, for example, a p-type dopant. The p-type dopant can be, but is not limited to, one of a quinine derivative, a metal oxide, and a cyano-group containing compound. For example, non-limiting examples of p-type dopants are quinone derivatives such as Tetracyanoquinodimethane (TCNQ), 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ), and the like; metal oxides such as tungsten oxide, molybdenum oxide, and the like; and cyano-containing compounds such as the following compound HT-D1, but are not limited thereto.
The hole transport region may further include a buffer layer.
The buffer layer may compensate for an optical resonance distance of light according to a wavelength of light emitted from the emission layer, and thus may improve efficiency.
An emission layer (EML) may be formed on the hole transport region by using vacuum deposition, spin coating, casting, an LB method, or the like. When the emission layer is formed using vacuum deposition or spin coating, conditions for deposition and coating may be similar to those for formation of the hole injection layer, although the conditions for deposition and coating may vary depending on the material used to form the emission layer.
The emissive layer may include a host and a dopant.
An organic photoelectric device according to an embodiment of the present invention includes a compound for an organic photoelectric device represented by chemical formula 1 alone, or a compound for an organic photoelectric device represented by chemical formula 1 as a first host and a carbazole-based compound as a second host.
The carbazole-based compound may be specifically represented by chemical formula a or may be composed of a combination of a moiety represented by chemical formula B and a moiety represented by chemical formula C.
In the chemical formulae a to C,
Ar3to Ar6Independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
m is an integer of 0 or 1,
two adjacent chemical formula B are independently CR combined with two chemical formula C to form a fused ring and not forming a fused ring of chemical formula BbAnd is and
Rband R7To R14Independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.
The biscarbazole represented by formula A may be, for example, a compound selected from [ group B ], and
the indolocarbazole composed of a combination of the moiety represented by formula B and the moiety represented by formula C may be, for example, a compound selected from [ group C ].
[ group B ]
[ group C ]
The first and second bodies described above can be used in various proportions to prepare various compositions. For example, the first body and the second body may be used in a weight ratio of 1:99 to 99:1, e.g., 10:90 to 90: 10. For example, the weight ratio may be 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4, or 5: 5. When the first and second hosts satisfy the weight ratio range, electron transport characteristics through the first host and hole transport characteristics through the second host may be balanced, thereby improving the light emitting efficiency and lifespan of the organic light emitting diode.
For example, the compound may be used as a light emitting material for an organic photoelectric device.
Herein, the light emitting material may be an organic compound as a host, and may further include at least one dopant. The dopant may be a red, green or blue dopant.
The dopant is mixed in a small amount to cause light emission, and may be generally a material such as a metal complex, which emits light by being excited to a triplet state or more multiple times. The dopant may be, for example, an inorganic, organic, or organic/inorganic compound, and one or more of them may be used.
The dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by formula Z, but is not limited thereto.
[ chemical formula Z ]
L2MX
In formula Z, M is a metal, and L and X are the same or different and are ligands for forming a coordination compound with M.
M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L and X can be, for example, bidentate ligands.
The thickness of the emitting layer may be
To
For example
To
When the thickness of the emission layer is within these ranges, the emission layer may have improved emission characteristics without a large increase in driving voltage.
Next, an electron transport region is disposed on the emission layer.
The electron transport region may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer.
For example, the electron transport region may have a structure of a hole blocking layer/an electron transport layer/an electron injection layer or an electron transport layer/an electron injection layer, but is not limited thereto. For example, the organic light emitting diode according to one embodiment of the present invention includes at least two electron transport layers in the electron transport region, and in this case, the electron transport layer contacting the emission layer is defined as an electron transport auxiliary layer.
The electron transport layer may have a single layer or a multi-layer structure including two or more different materials.
The electron transport region may include a compound for an organic photoelectric device represented by chemical formula 1. For example, the electron transport region may include an electron transport layer, and the electron transport layer may include a compound for an organic photoelectric device represented by chemical formula 1. More specifically, the electron transport auxiliary layer may include a compound for an organic photoelectric device represented by chemical formula 1.
The formation conditions of the hole blocking layer, the electron transport layer, and the electron injection layer of the electron transport region are referred to the formation conditions of the hole injection layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, but is not limited to, at least one of BCP, Bphen, and BAlq.
The hole blocking layer may have a thickness of
To
For example
To
When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have improved hole blocking capability without a large increase in driving voltage.
The electron transport layer may further include at least one of BCP, Bphen and Alq3, Balq, TAZ, and NTAZ below.
Alternatively, the electron transport layer may include at least one of compounds ET1 and ET2, but is not limited thereto.
The thickness of the electron transport layer may be
To
For example
To
When the thickness of the electron transport layer is within these ranges, the electron transport layer may have satisfactory electron transport ability without a large increase in driving voltage.
In addition to the above materials, the electron transport layer may further include a metal-containing material.
The metal-containing material can include a lithium (Li) complex, which can include, for example, the compounds ET-D1 (lithium quinolate, LiQ) or ET-D2.
In addition, the electron transport region may include an electron injection layer, which may facilitate injection of electrons from the anode.
The electron injection layer is disposed on the electron transport layer and may play a role of promoting electron injection from the cathode and ultimately improving power efficiency and is formed by using any material used in the related art without particular limitation, for example, LiF, Liq, NaCl, CsF, Li2O, BaO, and the like.
The electron injection layer may comprise a material selected from LiF, NaCl, CsF, Li2At least one of O, and BaO.
The electron injection layer may have a thickness of
To
Or
To
When the thickness of the electron injection layer is withinWithin these ranges, the electron injection layer can have satisfactory electron injection capability without a large increase in driving voltage.
The cathode is disposed on the organic layer. The material for the cathode may be a metal, an alloy, or a conductive compound having a low work function, or a combination thereof. Specific examples of the material for the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. In order to manufacture a top emission light emitting device, the anode 110 may be formed of, for example, Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO) in the form of a transmissive electrode.
Hereinafter, embodiments will be described in more detail with reference to examples. However, these examples are not to be construed in any way as limiting the scope of the invention.
The organic light emitting diode may be applied to an Organic Light Emitting Diode (OLED) display.
Hereinafter, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich co.ltd. or TCI inc.
Synthesis of intermediate I-2
The first step is as follows: synthesis of intermediate I-1
The 9-fluorene intermediate compound was synthesized by the following reaction procedure.
[ reaction scheme 1]
1, 3-dibromobenzene (1.0 equiv.) is placed in anhydrous THF (0.5M) in a 1000mL round flask, cooled in a dry ice acetone bath, and butyllithium (1.0 equiv., 2.5M in hexanes) is added slowly through a dropping funnel. After stirring the resulting mixture for 1 hour, fluorenone (1.0 equivalent) dissolved in anhydrous THF (0.5M) was slowly added thereto through a dropping funnel. Two hours after slowly heating the reaction to room temperature, the reaction was completed by adding an aqueous ammonium chloride solution thereto. Then, THF was removed under reduced pressure, and the reaction was dissolved again in dichloromethane and washed with water. After removal of the appropriate amount of organic solvent, the reaction was treated by column chromatography to obtain compound I-1 (70% yield).
Calculated C19H13BrO is C, 67.67; h, 3.89; br, 23.70; o, 4.74; measurement C, 67.67; h, 3.85; br, 23.73; o,4.76
The second step is as follows: synthesis of intermediate I-2
12.0g (35.5 mmol) of intermediate I-1 was placed in a 250mL round flask, which was then dissolved in an anhydrous benzene solution. After diluting the triflic acid (6.3mL, 2 equivalents) in 30mL of benzene, the diluted solution was added slowly to the reaction. The obtained reaction was heated and refluxed for 48 hours under a nitrogen stream. The reaction was washed with 0.5N aqueous sodium hydroxide solution and water, and after benzene was appropriately removed under reduced pressure, methanol (5 times that of benzene) was added thereto to obtain a crystalline solid, which was then filtered to obtain compound I-2(8.5g, 60% yield).
Calculated C25H17Br is C, 75.58; h, 4.31; br, 20.11; measurement C, 75.57; h, 4.30; br,20.13
Synthesis of intermediate I-4
Intermediate I-4 was synthesized by using 1, 2-dibromobenzene instead of 1, 3-dibromobenzene as the starting material in the first step for the synthesis of intermediate I-2, and then applying a second step thereto.
[ reaction scheme 2]
I-3: 65% yield
Calculated C19H13BrO is C, 67.67; h, 3.89; br, 23.70; o, 4.74; measurement C, 67.67; h, 3.85; br, 23.73; o,4.75
I-4: 50% yield
Calculated C25H17Br is C, 75.58; h, 4.31; br, 20.11; measured value C,75.57；H,4.31；Br,20.12
Synthesis of intermediate I-6
Intermediate I-6 was synthesized by using 1, 4-dibromobenzene instead of 1, 3-dibromobenzene as the starting material in the first step for the synthesis of intermediate I-2, and then applying a second step thereto.
[ reaction scheme 3]
I-5: 80% yield
Calculated C19H13BrO is C, 67.67; h, 3.89; br, 23.70; o, 4.74; measurement C, 67.67; h, 3.84; br, 23.74; o,4.75
I-6: 60% yield
Calculated C25H17Br is C, 75.58; h, 4.31; br, 20.11; measurement C, 75.57; h, 4.31; br,20.13
Synthesis of organic compounds
Synthesis example 1: synthesis of Compound 2-1
Compound 2-1, which is one specific example of the present invention, was synthesized by the following two steps.
[ reaction scheme 4]
The first step is as follows: synthesis of intermediate I-8 (Borate reaction)
50.0g (129 mmol) of intermediate I-7 (commercially available, TCI), 36g (142 mmol) of 4,4,4',4',5,5,5',5' -octamethyl-2, 2 '-bis-1, 3, 2-dioxaborolan, 3.15g (3.9 mmol) of [1,1' -bis (diphenylphosphino) ferrocene]Palladium (II) dichloride (Pd (dppf) Cl2) And 38g (387 mmol) of potassium acetate (KOAc) were put in 430mL (0.3M) of toluene in a 1000mL flask, followed by addition under a nitrogen stream at 110 deg.CThe heat was applied for 12 hours. The resulting mixture was added to 1000mL of methanol, and the crystallized solid was filtered and then treated by column chromatography to obtain intermediate I-8(47.7g, 85% yield).
Calculated C27H26BN3O2C, 74.49; h, 6.02; b, 2.48; n, 9.65; o, 7.35; measurement C, 74.47; h, 6.03; b, 2.47; n, 9.67; o,7.35
The second step is as follows: synthesis of Compound 2-1
11.9g (34.8 mmol) of intermediate I-2, 13.6g (30.0 mmol) of an arylboronate ester (arylboronate) I-8, 12.4g (90.0 mmol) of potassium carbonate, and 1.7g (1.5 mmol) of Pd (PPh)3)4(tetrakis (triphenylphosphine) palladium (0)) was placed in 50mL of water and 100mL of tetrahydrofuran in a 1000mL flask, followed by heating at 70 ℃ for 12 hours under a nitrogen stream. The resulting mixture was added to 500mL of methanol to crystallize the solid, then the solid was filtered, dissolved in dichlorobenzene, filtered with silica gel/celite, and then, after removing an appropriate amount of organic solvent, recrystallized with methanol to obtain compound 2-1(15.0g, 80% yield).
Calculated C46H31N3C, 88.29; h, 4.99; n, 6.72; measurement C, 88.27; h, 4.98; n,6.75
Synthesis example 2: synthesis of Compound 2-2
Compound 2-2, which is one specific example of the present invention, was synthesized by the following two steps.
[ reaction scheme 5]
The first step is as follows: synthesis of intermediate I-10 (boron addition reaction)
Intermediate I-10 was synthesized according to the same method as the synthesis of intermediate I-8 by using intermediate I-9(Ark Pharm, cas:77989-15-2) instead of intermediate I-7 (yield 60%).
CalculatedC27H26BN3O2C, 74.49; h, 6.02; b, 2.48; n, 9.65; o, 7.35; measurement C, 74.47; h, 6.03; b, 2.47; n, 9.68; o,7.34
The second step is as follows: synthesis of Compound 2-2
Compound 2-2 was synthesized (50% yield) according to the same method as the synthesis of Compound 2-1, by using intermediate I-10 instead of intermediate I-8.
Calculated C46H31N3C, 88.29; h, 4.99; n, 6.72; measurement C, 88.27; h, 4.98; n,6.75
Synthetic example 3: synthesis of Compounds 2-4
Compound 2-4 was synthesized by using intermediate I-4 according to the same method as the synthesis of compound 2-1.
Calculated C46H31N3C, 88.29; h, 4.99; n, 6.72; measurement C, 88.27; h, 4.98; n,6.75
Synthetic example 4: synthesis of Compounds 2-5
Compound 2-5 was synthesized according to the same method as the synthesis of compound 2-1, by using intermediate I-6.
Calculated C46H31N3C, 88.29; h, 4.99; n, 6.72; measurement C, 88.28; h, 4.98; n,6.76
Synthesis example 5: synthesis of Compounds 2-7
Compounds 2-7, which are one specific example of the present invention, were synthesized by the following three steps.
[ reaction scheme 6]
The first step is as follows: synthesis of intermediate I-12
Intermediate I-12 was synthesized (90% yield) according to the same method as the second step for synthesizing Compound 2-1, by using intermediate I-11(PharmaBlock, cas:1472062-94-4) and 3-chlorophenylboronic acid.
Calculated C27H18ClN3C, 77.23; h, 4.32; cl, 8.44; n, 10.01; measurement C, 77.23; h, 4.32; cl, 8.44; n,10.01
The second step is as follows: synthesis of intermediate I-13
Intermediate I-13 was synthesized (70% yield) by using intermediate I-12 according to the same method as the first step in synthesizing Compound 2-1.
Calculated C33H30BN3O2C, 77.50; h, 5.91; b, 2.11; n, 8.22; o, 6.26; measurement C, 77.52; h, 5.91; b, 2.10; n, 8.21; o,6.26
The third step: synthesis of Compounds 2-7
Compound 2-7 was synthesized (80% yield) by using intermediate I-13 according to the same method as the second step for synthesizing Compound 2-1.
Calculated C52H35N3C, 88.99; h, 5.03; n, 5.99; measurement C, 88.97; h, 5.06; n,5.98
Synthetic example 6: synthesis of Compounds 2-12
Compounds 2-12, which are one specific example of the present invention, were synthesized by the following three steps.
[ reaction scheme 7]
The first step is as follows: synthesis of intermediate I-14
Intermediate I-14 was synthesized by using intermediate I-7 and 3-chlorophenylboronic acid according to the same method as the second step for synthesizing compound 2-1 (yield 80%).
Calculated C27H18ClN3C, 77.23; h, 4.32; cl, 8.44; n, 10.01; measurement C, 77.23; h, 4.32; cl, 8.44;N,10.01
the second step is as follows: synthesis of intermediate I-15
Intermediate I-15 was synthesized by using intermediate I-14 according to the same method as the first step in synthesizing Compound 2-1 (yield of 70%).
Calculated C33H30BN3O2C, 77.50; h, 5.91; b, 2.11; n, 8.22; o, 6.26; measurement C, 77.50; h, 5.90; b, 2.11; n, 8.21; o,6.26
The third step: synthesis of Compounds 2-12
Compound 2-12 was synthesized (80% yield) by using intermediate I-15 according to the same method as the second step for synthesizing Compound 2-1.
Calculated C52H35N3C, 88.99; h, 5.03; n, 5.99; measurement C, 88.99; h, 5.03; n,5.99
Synthetic example 7: synthesis of Compounds 3-9
Compounds 3 to 9, which are one specific example of the present invention, were synthesized by the following three steps.
[ reaction scheme 8]
The first step is as follows: synthesis of intermediate I-17
30.1g (100 mmol) of intermediate I-16(Aurora Building Blocks, cas:1155152-53-6), 25.6g (210 mmol) of phenylboronic acid, 41.5g (300 mmol) of potassium carbonate, and 3.5g (3.0 mmol) of Pd (PPh)3)4(tetrakis (triphenylphosphine) palladium (0)) was placed in a 1000mL flask in 200mL of tetrahydrofuran and 100mL of water, and then heated at 70 ℃ under a nitrogen stream for 12 hours. The resulting mixture was added to 600mL of methanol to crystallize the solid, and the solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and then, after removing an appropriate amount of organic solvent, recrystallized through methanol to obtain intermediate I-17(27.4g, 80% yield).
Calculated C22H15ClN2C, 77.08; h, 4.41; cl, 10.34; n, 8.17; measurement C, 77.06; h, 4.43; cl, 10.34; n,8.17
The second step is as follows: synthesis of intermediate I-18
Intermediate I-18 was synthesized (75% yield) by using intermediate I-17 according to the same method as the first step in synthesizing Compound 2-1.
Calculated C28H27BN2O2C, 77.43; h, 6.27; b, 2.49; n, 6.45; o, 7.37; measurement C, 77.44; h, 6.26; b, 2.48; n, 6.46; o,7.37
The third step: synthesis of Compounds 3-9
Compounds 3-9 were synthesized (80% yield) by using intermediate I-18 according to the same method as the second step for synthesizing Compound 2-1.
Calculated C47H32N2C, 90.35; h, 5.16; n, 4.48; measurement C, 90.34; h, 5.17; n,4.49
Synthesis example 8: synthesis of Compounds 3-14
Compounds 3 to 14, which are one specific example of the present invention, were synthesized by the following three steps.
[ reaction scheme 9]
The first step is as follows: synthesis of intermediate I-19
8g (30 mmol) of intermediate I-18, 4.2mL (36 mmol) of 1-bromo-3-chlorobenzene, 13.7g (90 mmol) of potassium carbonate, and 1.15g (1.0 mmol) of Pd (PPh)3)4(tetrakis (triphenylphosphine) palladium (0)) was added to 100mL of tetrahydrofuran and 50mL of water in a 1000mL flask, followed by heating at 70 ℃ under a nitrogen stream for 12 hours. The resulting mixture was added to 500mL of methanol to crystallize a solid, and the solid was filteredDissolved in dichlorobenzene, filtered through silica gel/celite, and then, after removal of a certain amount of organic solvent, recrystallized from methanol to obtain intermediate I-19(9.1g, 70% yield).
The second step is as follows: synthesis of intermediate I-20
Intermediate I-20 was synthesized (75% yield) by using intermediate I-19 according to the same method as the first step in synthesizing Compound 2-1.
Calculated C34H31BN2O2C, 80.00; h, 6.12; b, 2.12; n, 5.49; o, 6.27; measurement C, 80.00; h, 6.13; b, 2.12; n, 5.49; o,6.26
The third step: synthesis of Compounds 3-14
Compounds 3-14 were synthesized (80% yield) by using intermediate I-20 according to the same method as the second step for synthesizing Compound 2-1.
Calculated C53H36N2C, 90.83; h, 5.18; n, 4.00; measurement C, 90.84; h, 5.17; n,4.00
Synthetic example 9: synthesis of Compounds 4-9
Compounds 4 to 9 were synthesized according to the same method as that for the synthesis of compounds 3 to 9 of Synthesis example 7, by using intermediate I-21(Aurora Building Blocks, cas: 145903-35-1).
[ reaction scheme 10]
Calculated C47H32N2C, 90.35; h, 5.16; n, 4.48; measurement C, 90.34; h, 5.17; n,4.47
Synthetic example 10: synthesis of Compounds 4-14
Compounds 4-14 were synthesized according to the same method as the synthesis of compounds 2-12, by using intermediate I-24(Apichemical, cas: 1262866-93-2).
Calculated C53H36N2C, 90.83; h, 5.18; n, 4.00; measurement C, 90.84; h, 5.17; n,4.00
Synthetic example 11: synthesis of Compound 5-1
Compound 5-1, which is one specific example of the present invention, was synthesized by the following three steps.
[ reaction scheme 11]
The first step is as follows: synthesis of intermediate I-25
Intermediate I-25 (90% yield) was synthesized according to the same method as the second step for synthesizing Compound 2-1, using intermediate I-24(Apichemical, cas:1262866-93-2) and 3-chlorophenylboronic acid.
Calculated C20H13ClN2C, 75.83; h, 4.14; cl, 11.19; n, 8.84; measurement C, 75.84; h, 4.16; cl, 11.17; n,8.85
The second step is as follows: synthesis of intermediate I-26
Intermediate I-26 was synthesized (70% yield) by using intermediate I-25 according to the same method as the first step in synthesizing Compound 2-1.
Calculated C32H29BN2O2C, 79.34; h, 6.03; b, 2.23; n, 5.78; o, 6.61; measurement C, 79.33; h, 6.03; b, 2.23; n, 5.78; o,6.62
The third step: synthesis of Compound 5-1
Compound 5-1 was synthesized (80% yield) by using intermediate I-26 according to the same method as the second step for synthesizing Compound 2-1.
Calculated C51H34N2C, 90.77; h, 5.08; n, 4.15; measurement C, 90.77; h, 5.08; n,4.14
Synthetic example 12: synthesis of Compounds 5-13
Compounds 5 to 13, which are one specific example of the present invention, were synthesized by the following three steps.
[ reaction scheme 12]
The first step is as follows: synthesis of intermediate I-29
Intermediate I-29 (80% yield) was synthesized according to the same method as the second step for synthesizing Compound 2-1, by using 3-bromo-3' -chlorobiphenyl of intermediate I-27(Apichemical, cas:29874-83-7) and intermediate I-28(Oakwood Chemical, cas: 844856-42-4).
Calculated C26H17ClN2C, 79.48; h, 4.36; cl, 9.02; n, 7.13; measurement C, 79.48; h, 4.35; cl, 9.02; n,7.14
The second step is as follows: synthesis of intermediate I-30
Intermediate I-30 was synthesized (70% yield) by using intermediate I-29 according to the same method as the first step in synthesizing Compound 2-1.
Calculated C32H29BN2O2C, 79.34; h, 6.03; b, 2.23; n, 5.78; o, 6.61; measurement C, 79.34; h, 6.03; b, 2.23; n, 5.77; o,6.61
The third step: synthesis of Compounds 5-13
Compounds 5-13 were synthesized (77% yield) by using intermediate I-30 according to the same method as that for the synthesis of compound 2-1.
Calculated C51H34N2C, 90.77; h, 5.08; n, 4.15; measurement C, 90.77; h, 5.08; n,4.14
Synthetic example 13: synthesis of Compounds 6-9
Compounds 6 to 9, which are one specific example of the present invention, were synthesized by the following four steps.
[ reaction scheme 13]
The first step is as follows: synthesis of intermediate I-32
Intermediate I-32 was synthesized (80% yield) according to the same method as the second step for synthesizing Compound 2-1, by using intermediate I-31(TCI) and 3-chlorophenylboronic acid (1 equivalent). Here, the reaction was carried out under the same conditions except that the temperature was changed to 60 ℃.
Calculated C14H8Cl2N2C, 61.12; h, 2.93; cl, 25.77; n, 10.18; measurement C, 61.12; h, 2.93; cl, 25.77; n,10.18
The second step is as follows: synthesis of intermediate I-33
Intermediate I-33 was synthesized (60% yield) by using intermediate I-32 and 4-biphenylboronic acid according to the same method as the second step of synthesizing compound 2-1.
Calculated C26H17ClN2C, 79.48; h, 4.36; cl, 9.02; n, 7.13; measurement C, 79.48; h, 4.36; cl, 9.03; n,7.13
The third step: synthesis of intermediate I-34
Intermediate I-34 was synthesized according to the same method as the first step in the synthesis of intermediate I-33 (80% yield).
Calculated C32H29BN2O2C, 79.34; h, 6.03; b, 2.23; n, 5.78; o, 6.61; measurement C, 79.34; h, 6.03; b, 2.23; n, 5.78; o,6.61
The fourth step: synthesis of Compounds 6-9
Compounds 6-9 (75% yield) were synthesized according to the same method as the second step for synthesizing Compound 2-1, by using intermediate I-34.
Calculated C51H34N2:C,90.77；H,5.08；N,4.15; measurement C, 90.78; h, 5.07; n,4.15
Synthesis of Compounds of reference examples
Reference Compound 1(depending on the effect of the presence or absence of the linking group)
[ reaction scheme 14]
Reference compound 1 was synthesized according to the same method as that for synthesizing compound 2-1 of example 1 (60% yield).
Calculated C40H27N3C, 87.40; h, 4.95; n, 7.64; measurement C, 87.41; h, 4.95; n,7.64
Reference Compound 2(Effect of alkyl group substitution in 9, 9-Diphenylfluorene)
[ reaction scheme 15]
Reference compound 2 was synthesized according to the same method as that for the intermediate I-2 and compound 2-1 of the synthesis examples (30% yield).
Calculated C50H39N3C, 88.07; h, 5.77; n, 6.16; measurement C, 88.08; h, 5.76; n,6.15
Reference Compound 3(Ar having electronic Properties)1Effect of a substituent without additional substituent such as aryl group and the like)
[ reaction scheme 16]
Reference compound 3 was synthesized by Suzuki reaction (Suzuki reaction) for the synthesis of compound 2-1 by using an intermediate of reference compound 1 and 2- (4-bromophenyl) -1,3, 5-triazine (Aurora Building Blocks, cas:1369015-30-4) (65% yield).
Calculated C34H23N3C, 86.23; h, 4.90; n, 8.87; measurement C, 86.24; h, 4.89; n,8.87
Fabrication of organic light emitting diode 1: separate body
Example 1
By using the compound 2-1 according to Synthesis example 1 as a host and Ir (PPy)3As a dopant, an organic light emitting diode is manufactured.
Will be provided with
Thick ITO is used as the anode, and
thick aluminum (Al) was used as the cathode. Specifically, the organic light emitting diode is manufactured by the following method: will have a capacitance of 15 Ω/cm2The ITO glass substrate of sheet resistance of (1) was cut into a size of 50 mm. times.50 mm. times.0.7 mm, it was ultrasonically cleaned in acetone, isopropyl alcohol, and pure water for 15 minutes, respectively, and then it was cleaned with UV ozone for 30 minutes.
At 650X 10-7Forming N4, N4 '-di (naphthalene-1-yl) -N4, N4' -biphenylyl-4, 4 '-diamine (NPB) (80nm) on a substrate by depositing N4, N4' -di (naphthalene-1-yl) -N4, N4 '-biphenylyl-4, 4' -diamine (NPB) at a deposition rate of 0.1 to 0.3nm/s under a vacuum degree of Pa
A thick hole transport layer. Subsequently, according to Synthesis example 1, by using Compound 2-1 under the same vacuum deposition conditions as described above, a layer serving as an emission layer was formed
Thick film and, here, simultaneous deposition of Ir (PPy) as phosphorescent dopant3. Here, the phosphorescent dopant is deposited in an amount of 10 wt% by adjusting the deposition rate based on 100 wt% of the total amount of the emission layer.
Forming a hole blocking layer on the emission layer by depositing bis (2-methyl-8-hydroxyquinoline) -4- (phenylphenol) aluminum (BAlq) under the same vacuum deposition conditions as described above
A thick film. Subsequently, as an electron transport layer, Alq3 was formed by deposition under the same vacuum deposition conditions as described above
A thick film. On the electron transport layer, LiF and Al were sequentially deposited as cathodes, thereby manufacturing an organic photoelectric device.
The organic photoelectric device has ITO/NPB (80nm)/EML (Compound 2-1(90 wt%) + Ir (PPy)3(10 wt%), 30nm)/Balq (5nm)/Alq3(20nm)/LiF (1nm)/Al (100 nm).
Examples 2 to 8
Organic light emitting diodes according to examples 2 to 8 were manufactured according to the same method as example 1 by using compounds 2-2, 2-4, 2-5, 2-7, 2-12, 3-9, and 4-9 of synthesis examples 2 to 7 and 9, respectively, instead of compound 2-1 of synthesis example 1.
Comparative example 1
An organic light emitting diode was manufactured according to the same method as example 1, except that CBP having the following structure was used instead of compound 2-1 of synthesis example 1.
Reference examples 1 to 3
Organic light emitting diodes according to reference examples 1 to 3 were manufactured according to the same method as example 1, except that the reference compounds 1 to 3 according to the reference examples were respectively used instead of the compound 2-1 according to synthesis example 1.
NPB, BAlq, CBP, and ir (ppy)3 used in the organic light emitting diode respectively have the following structures.
Evaluation of
The current density variation, luminance variation, and luminous efficiency of each of the organic light emitting diodes according to examples 1 to 8, comparative example 1, and reference examples 1 to 3 were measured.
Specific measurement methods are as follows, and the results are shown in table 1.
(1) Measurement of current density variations depending on voltage variations
The obtained organic light emitting diode was measured with respect to a current value flowing in the unit device by using a current voltmeter (Keithley 2400) while increasing the voltage from 0V to 10V, and the measured current value was divided by the area to provide a result.
(2) Measurement of brightness variation depending on voltage variation
The luminance was measured by using a luminance meter (Minolta Cs-1000A) while increasing the voltage of the organic light emitting diode from 0 to 10V.
(3) Measurement of luminous efficiency
The same current density (10 mA/cm) was calculated by using the luminance, current density, and voltage (V) from items (1) and (2)2) Lower current efficiency (cd/A).
(4) Measurement of lifetime
In the average luminance (cd/m)2) Maintained at 5000cd/m2At the same time, the lifetime was obtained by measuring the time for the current efficiency (cd/A) to decrease to 90%.
[ Table 1]
Referring to table 1, the organic light emitting diodes according to examples 1 to 8 show comparable or superior efficiency and improved life characteristics compared to the organic light emitting diodes according to comparative example 1 and reference examples 1 to 3. In particular, the organic light emitting diodes according to examples 2 to 6 exhibited excellent driving voltage and simultaneously excellent efficiency and lifetime, which is a positive effect of introducing a linker, compared to the organic light emitting diode according to reference example 1.
As described above, when a linking group is included in a substituent having a 9, 9-diphenylfluorene structure and electronic characteristics, the linking group may increase flexibility of the compound, thus exerting excellent morphological characteristics thereto, which may play an important role in realizing high efficiency, long life, and low driving voltage of an organic photoelectric device.
Further, a substituent having an electronic property necessarily includes another substituent, and thus the weakest part of the heterocycle can be protected, obtaining a heat resistance increasing effect as compared with a substituent having an electronic property but not substituted. Further, a substituent having electronic characteristics and including another substituent exhibits excellent heat-resistant stability as compared with alkyl substitution, and the lifetime of the device is remarkably improved in addition to heat and electric stability. This is the reason why examples 1 to 8 are superior to reference examples 2 and 3.
Fabrication of organic light emitting diode 2: mixed body
Example 9
Ultrasonic washing with distilled water of ITO (indium tin oxide) -coated glass
A thick film glass substrate. After washing with distilled water, the glass substrate is ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then, moved toThe plasma cleaner was cleaned for 10 minutes by using oxygen plasma and moved to the vacuum depositor. Using the obtained ITO transparent electrode as an anode, Compound A was deposited by vacuum deposition to form an ITO substrate
A thick hole injection layer, and by depositing a compound B to
Thickness and compound C to
Thick, and a hole transport layer is formed on the injection layer. Compound 2-1 according to Synthesis example 1 and Compound B-1 according to Synthesis example 26 both as a second host Compound and at the same time as a host, and tris (2-phenylpyridine) iridium (III) [ Ir (ppy)3]Formed on the hole transport layer with a doping amount of 10 wt% as a dopant
A thick emissive layer. Herein, compound 2-1 and compound B-1 were used in a 1:1 ratio.
Subsequently, compound D and Liq were simultaneously vacuum-deposited at a ratio of 1:1 to form on the emission layer
Thick electron transport layer, and subsequent vacuum deposition of Liq on the electron transport layer
And Al
To form a cathode to fabricate the organic light emitting diode.
The organic light emitting diode has a layered structure of five organic thin films, specifically,
ITO/Compound A
Compound B
Compound C
EML [ Compound 1: b-1 Ir (ppy)3＝45wt％:45wt％:10wt％]
Compound D Liq
/Liq
/Al
The structure of (1).
A compound A: n4, N4' -biphenyl-N4, N4' -bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4, 4' -diamine
Compound B: 1,4,5,8,9, 11-hexaazatriphenylene-hexacarbonitrile (HAT-CN),
compound C: n- (biphenyl-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine
Compound D: 8- (4- (4, 6-bis (naphthalen-2-yl) -1,3, 5-triazin-2-yl) phenyl) quinoline
Example 10
An organic light emitting diode was manufactured according to the same method as example 9, except that the compound 2-1 and the compound B-31 were used at a weight ratio of 1: 1.
Example 11
An organic light emitting diode was manufactured according to the same method as example 9, except that the compounds 2-7 and the compound B-31 were used at a weight ratio of 1: 1.
Example 12
An organic light emitting diode was manufactured according to the same method as example 9, except that the compounds 2-12 and the compound B-31 were used at a weight ratio of 1: 1.
Example 13
An organic light emitting diode was manufactured according to the same method as example 9, except that the compound 2-1 and the compound C-1 were used at a weight ratio of 1: 1.
Example 14
An organic light emitting diode was manufactured according to the same method as example 9, except that the compound 3-9 and the compound B-31 were used at a weight ratio of 1: 1.
Comparative example 2
An organic light emitting diode was manufactured according to the same method as example 9, except that CBP was used as a single body.
Reference examples 4 to 6
Each of the organic light emitting diodes according to reference examples 4 to 6 was manufactured according to the same method as example 9, except that the reference compounds 1 to 3 were used as a single body.
Evaluation of
The light emitting efficiency and the life span characteristics of each of the organic light emitting diodes according to examples 9 to 14, comparative example 2, and reference examples 4 to 6.
The specific measurement methods were as described above except for "(4) measurement of lifetime", and the results are shown in table 2.
(4) Measurement of lifetime
In the average luminance (cd/m)2) Maintained at 6000cd/m2Meanwhile, the lifetime was obtained by measuring the time for the current efficiency (cd/A) to decrease to 97%.
[ Table 2]
Referring to Table 2, the organic light emitting diodes according to examples 9 to 14 showed significantly improved light emitting efficiency and life span characteristics, compared to the organic light emitting diodes according to comparative example 2 and reference examples 4 to 6.
Manufacture of organic light-emitting diodes 3
Example 15
Washing with distilled water of ITO (indium tin oxide) -coated as
A thick film glass substrate. After washing with distilled water, the glass substrate is ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc., and dried, moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then moved to a vacuum depositor. The obtained ITO transparent electrode was used as an anode, and formed by vacuum deposition of Compound A on an ITO substrate
A thick hole injection layer and formed by depositing a compound B to
Thickness and compound C to
Thick to form a hole transport layer on the injection layer. Then, BH113 and BD370(Dealer: SFC Inc.) as blue fluorescence emitting hosts and dopants at a dopant concentration of 5 wt% were formed thereon by vacuum deposition
A thick emissive layer. Vacuum depositing compound 2-1 on the emissive layer to form
A thick electron transport assisting layer. By using the material of formula I alone or in combination with groups B, C, D, and ETo form an electron transport assisting layer. Formation on the electron transport auxiliary layer by simultaneous vacuum deposition of Compound D and Liq in a weight ratio of 1:1
A thick electron transport layer and depositing Liq to
Thickness and Al to
Thick to form a cathode on the electron transport layer, thereby fabricating an organic light emitting diode. The organic light emitting diode has a structure of 5 organic thin film layers, and specifically, ITO/Compound A
Compound B
Compound C
/EML[BH113:BD370＝95:5(wt:wt)]
Compound 2-1
Compound D Liq
/Al
(Compounds A, B, C and D are the same as those used in the organic light-emitting diode 2)
Examples 16 to 23
Organic light emitting diodes of examples 16 to 23 were manufactured according to the same method as example 15, except that compound 2-2, compound 2-4, compound 2-12, compound 3-14, compound 4-14, compound 5-1, compound 5-13, and compound 6-9 were used instead of compound 2-1, respectively.
Reference example 7
An organic light-emitting diode was manufactured according to the same method as example 15, except that the reference compound 1 was used instead of the compound 2-1.
Comparative example 3
An organic light emitting diode was manufactured according to the same method as example 15, except that the electron transport assisting layer was not used.
Evaluation of
The current density variation, luminance variation, and luminous efficiency of each of the organic light emitting diodes according to examples 15 to 23, reference example 7, and comparative example 3 were measured.
The specific measurement methods were as described above except for "(4) measurement of lifetime", and the results are shown in table 3.
(4) Measurement of lifetime
The T97 life time of the organic light emitting diodes according to example 15 to example 23, reference example 7, and comparative example 3 was measured to have an emission of 750cd/m2As the initial luminance (cd/m)2) And their time-dependent luminance decrease was measured with a Polanonix lifetime measurement system relative to the initial luminance (cd/m)2) The time when their brightness dropped to 97%.
[ Table 3]
Referring to table 3, the organic light emitting diodes of examples 15 to 23 simultaneously showed improved light emitting efficiency and life span characteristics, compared to the organic light emitting diode of comparative example 3. In addition, the organic light emitting diodes of examples 15 to 23 showed greatly improved life span characteristics compared to the organic light emitting diode of reference example 7.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not to be limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The above embodiments are therefore to be understood as illustrative and not restrictive in any way.
Claims (9)
1. An organic compound represented by chemical formula 1:
[ chemical formula 1]
Wherein, in chemical formula 1,
R1to R4Independently of each other is hydrogen or deuterium,
n1 is 5, and
n2 to n4 are independently 4,
Ar1represented by one selected from chemical formulas 2 to 6:
wherein, in chemical formulas 2 to 6,
R5to R12Independently a C6 to C20 aryl group,
wherein L is represented by one selected from the group consisting of chemical formula L-1 to chemical formula L-7:
wherein, in the chemical formulae L-1 to L-7,
R13to R17Independently a C1 to C20 alkyl group or a C6 to C20 aryl group,
m1 to m3 and m5 are independently an integer of 0 to 4, and
m4 is an integer of 0 to 3.
2. The organic compound of claim 1, wherein the C6 to C20 aryl group is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, or a pyrenyl group.
3. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of chemical formula 2-1 to chemical formula 2-24, chemical formula 3-1 to chemical formula 3-24, chemical formula 4-1 to chemical formula 4-24, chemical formula 5-1 to chemical formula 5-23, and chemical formula 6-1 to chemical formula 6-23:
4. an organic photoelectric device comprises
An anode and a cathode facing each other, and
at least one organic layer between the anode and the cathode,
wherein the organic layer comprises the organic compound according to any one of claim 1 to claim 3.
5. The organic optoelectronic device of claim 4, wherein the organic layer comprises
Hole transport layer, electron transport layer, and
an emissive layer between the hole transport layer and the electron transport layer, and
the organic compound is contained in the emission layer.
6. The organic photoelectric device according to claim 5, wherein the organic compound is used as a host material in the emission layer.
7. The organic photoelectric device according to claim 6, wherein the emission layer comprises the organic compound and a second organic compound as host materials, and the second organic compound comprises at least one of a compound represented by formula A and a compound composed of a combination of a moiety represented by formula B and a moiety represented by formula C:
[ chemical formula A ]
Wherein, in the chemical formulas A to C,
Ar3to Ar6Independently a C6 to C30 aryl group, or a C2 to C30 heteroaryl group,
m is an integer of 0 or 1,
adjacent two of formula B are independently CR combined with two of formula C to form fused rings and not form fused rings of formula BbAnd is and
Rband R7To R14Independently hydrogen, deuterium, a C1 to C10 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group.
8. The organic optoelectronic device of claim 4, wherein the organic layer comprises
A hole-transporting layer, which is a hole-transporting layer,
an electron-transporting layer, which is a layer of a metal,
an emissive layer between the hole transport layer and the electron transport layer, and
an electron transport auxiliary layer or a hole blocking layer between the emission layer and the electron transport layer, and the organic compound is contained in the electron transport auxiliary layer.
9. A display device comprising the organic photoelectric device according to claim 4.
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| KR102160270B1 (en) | 2017-10-20 | 2020-09-25 | 삼성에스디아이 주식회사 | Composition for organic optoelectric device and organic optoelectric device and display device |
| EP3483153A1 (en) * | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine group, fluorene-group and aryl group and their use in organic electronic devices |
| KR102044943B1 (en) | 2018-05-28 | 2019-11-14 | 삼성에스디아이 주식회사 | Compound, composition and organic optoelectronic device and display device |
| CN112409243A (en) * | 2019-08-23 | 2021-02-26 | 支志明 | Tetradentate ligand, gold (III) complex, and preparation method and application thereof |
| JP7361564B2 (en) * | 2019-10-23 | 2023-10-16 | 東ソー株式会社 | Triazine compounds containing Group 14 elements |
| CN114641470A (en) * | 2019-12-20 | 2022-06-17 | 株式会社Lg化学 | Compound and organic light emitting device including the same |
| CN112321585B (en) * | 2020-10-30 | 2022-04-22 | 华南理工大学 | Asymmetric substituted diphenyl pyridine compound and preparation and application thereof |
| CN112830900B (en) * | 2021-01-07 | 2022-12-02 | 吉林奥来德光电材料股份有限公司 | Phosphorescent compound, method of preparing the same, and organic electroluminescent device comprising the same |
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